OK, this is an unusual one.
A couple of months back i met this guy, i saw him at this bar, he instantly caught my attention, he's just so handsome! -- nice styled hair, Greek god abs and pecs and charming gray eyes. So i spent the rest of the night chatting him up and trying my charms on him, and by the end of the night i gave him my number and he left me drooling like a high school girl. And so we went out. While at the beginning i was just looking for a quick fling like most boys in their twenties, this seemed to take a more serious turn, but i didn't care.
With a couple of dates past and having come to know each other well, i started making several bold sexual advances, and he would always deflect them. So i started to have my suspicions, and eventually we got a moment in private at his place to talk about that and the conversation took a turn i never saw coming. It turns out the reason he wouldn't respond to my advances is the fact that he is a female to male transsexual. I was prepared for many situations but didn't know how to react to that, and so we talked about that for several hours; he said that he was too afraid of the sex reassignment surgery and besides had heard it didn't have such good results, so eventually i told him that i love him and that it doesn't matter. Then we stepped into the bedroom. I gotta say i love him and all but it was weird, it took some concentration to actually perform, something that had never happened before, but above all i enjoyed it and instead of concentrating on the state of his genitals i just concentrated on who i was with.
So a couple of days later i learned that a good friend of mine is a good friend of his too. He said he had not said a word [about his being a trans man] because he didn't want it to get in the way of a possible relationship. He also understood how the sex could get awkward, but i said that i couldn't tell him that. Truth is every time we have sex i must concentrate beforehand, and even though i enjoy it and it's been good so far i just can't seem to get "ready" without a little mental preparation. I truly love him and i don't want that to get in the way. I mean the rest of his body is clearly and beautifully manly, and i don't feel like me or anyone is in a position to force him into the [sex realignment] procedure.
It's just, i don't want this to get in the way as much as it does. I also do not have that much knowledge about the transsexual community, and it seems that female to males are harder to learn about than the other way around...
To finish i just want to know if there is any case like this that you know of. I have never known another relationship like this and i want it to go nicely. I mean the sex seems to be the only problem, and he hasn't so far known that it is. I mean it's something new to me, and i enjoy it but it still causes some trouble in my head, i just don't know...
Okay, for someone born biologically female to be convincingly masculine, they have to have some procedures of some sort done, even if it's just taking certain hormones, so your boyfriend must have had some work on his body. I take that the problem you have is that he's held on to his vagina instead of getting an artificial penis, which is expensive, and apparently not too convincing. This is fairly common among Trans Men. Since a vagina is so utterly feminine in nature, and gay men are generally attracted to everything that's masculine, I can certainly understand why the sexual experience seems strange to you. You're a gay man who's used to dick, so the whole situation seems a little bizarre and unreal. Yet you also love the guy and seem to be capable of getting beyond your initial -- for lack of a better word -- queasiness. As weeks go by you will probably become more and more comfortable with this situation, especially if you truly see him as a man and if both of you are in love with each other. If you never quite get used to it, then you both may have to face the fact that you just want and need a guy with a penis and that's that. [You can also try alternate sexual positions. If you're a top is your boyfriend willing to be a bottom on the, ahem, other end? If you have to make adjustments, so can he.]
I don't pretend to be an expert on transsexuality so I would suggest searching out web sites devoted to the subject where you can find out more and also possibly get in touch with other gay guys who are dating trans men. I know they exist. While trans men generally wind up dating or in relationships with other trans men -- or trans women, depending on their sexual orientation -- I believe it has become more commonplace of late for transsexuals to have relationships with non-transsexuals. Your situation is still unusual, perhaps, but not that unusual.
In the meantime, I'm not so certain it's a good idea for you to keep from your boyfriend the fact that you're not quite adjusting to the reality of his physical being. He needs to know that there is a problem, and maybe he can help you with it. It's better that he know now instead of finding out after he's hopelessly in love and you realize that you just can't make a complete adjustment.
On the other hand, sometimes love does conquer all.
I suggest you read another post on this blog regarding this very situation, as well as the several comments that follow it.